Can't Bet With Love
by Jessica Renee
Summary: Rory & Tristan vaguely heard of each other at Chilton. Now, 3 years later, they both go to Yale. A bet is put into place with Rory as the target. As Tristan tries to get her to fall for him, will he do the unthinkable and fall for her instead?
1. A Bet is Made

_10/13/05—just did a major rewrite. Lots of changes so if you read it before, check it out._

_Also, remember, this story is AU. Tristan and Rory _did_ go to Chilton together, but he never called her Mary and nothing happened between them unless otherwise stated. So I'd say in this story, Tristan went to Chilton with Rory for a couple of months and during sophomore year, the break-in to the safe happened, sending him to military school._

**Can't Bet with Love**

Part 1: _a bet is made._

Tristan Dugray sat in the coffee shop on Yale's campus with his three closest friends: Erik Hansen, Charlie Richards, and Michael Pratt. He normally wouldn't have been able to get into Yale if it hadn't been for his parents, who pulled a few strings. Erik and Charlie were the same. Guys with rich parents that normally wouldn't be able to get into an ivy-league school like Yale. Michael, on the other hand, had received almost a full scholarship to Yale, as his family wasn't nearly as well off as the others.

It wasn't that Tristan couldn't get into Yale, though. If he had tried, he could have earned a scholarship just like Erik, but instead he'd spent most of his high school years goofing off, spending more time with his friends than with his schoolwork. Well, it was more like spending _all_ of his time with his friends and leaving no time for schoolwork. And that was exactly how he planned to go through college.

"Whoa, babe standing at the cash register," Erik said.

He was always point out some girl that he found hot, wherever they went. Erik never went after the girls since he had a serious girlfriend, but he always said that didn't

Tristan didn't understand how Erik's girlfriend, Mallory King, could stand the fact that Erik checked out other girls. All of his ex-girlfriends would get really mad if he even as so much _looked_ at a girl—even if it was to order some coffee, dinner, or something like that. Erik said Mallory wasn't worried because she knew that Erik really loved her—which Tristan knew that he did. Whenever Erik was with Mallory, he focused on her and only her; not even bothering to look at any other girls. He even talked about Mallory all the time and he, Charlie, and Michael always teased him that he was whipped.

"I could get her," Charlie said.

"Sure you could," Tristan said, rolling his eyes. He knew that Charlie was all talk, no action. Charlie always said that he could get any girl, but he never did anything about it, whereas Tristan would say it and then would actually _get_ the girl. He liked to think that he was both talk _and_ action.

"I'd like to see you try and get her," Charlie said. "You think that you're the gift to all woman. Like every single woman would come to you when you snap your fingers."

Tristan rolled his eyes once again, shaking his head. "I'm not the Fonzi, I don't have to snap my fingers. They just come to me."

"Man, do you seriously think that you could get any girl?" Michael asked, leaning forward in his seat.

"I bet that you can't name one girl that I couldn't get," Tristan said with a smug smile. He knew that he was good looking and that many girls liked him.

Michael glanced at the door, his eyes following the pair that just walked in.

Tristan followed his line of sight, focused on two girls. They looked familiar, particularly the shorter of the two. She had long, light brownish blonde hair that reached about halfway down her back. Her eyes were dark; her mouth was set in an even line. Her name was on the tip of his tongue—she'd gone to school with him prior to Yale.

The other girl stood at about 5'7" with chocolate brown hair, falling into layers, just a bit shorter than her friend's. Her eyes were vivid blue, ones that he could see even across the room; a smile crossed her lips, a cleft appearing in her chin; her cheeks painted with a light dusty rose blush. While she looked familiar, he couldn't place her as well as he could place the other—and she didn't look like someone that he'd be able to forget all that easily.

"Rory Gilmore," Michael announced, noticing that Tristan was looking at her as well. "She's in my English class and I'll admit this, I tried to ask her out, numerous times might I add, but she declined every single offer."

Tristan looked up at the two girls again. _Rory Gilmore_. He repeated the name over and over in his head before he finally recognized that name. She had gone to Chilton with him. That was until he had gone to military school for trying to break into a safe that belonged to one of his friend's parents, along with that friend and another friend. After some consideration, he determined the other girl to be Paris Gellar, a girl that he had known since kindergarten.

"I could get her," Tristan said, understanding the challenge in Michael's voice. Although Michael was a bit of a brain, Tristan had to admit that he was up there in the look departments and his though the number of dates he had paled in comparison to Tristan's, his line of girls wasn't short.

"I'd like to see you try," Michael smirked. "The girl is practically an angel; I hear she's a virgin."

"I still know that I could get her," Tristan said. It wasn't like he'd never dated and "broken" other virgins before. "Not only to go out with but also…" he trailed off. His friends knew what he was talking about so there was no need to finish his sentence.

"I don't think Tristan could get Rory Gilmore," Charlie said, although he'd never heard of her before today. "She seems like a _girl_ who'd want a long-lasting relationship." Charlie stressed the word "girl" with a smirk. "And a long-term relationship to Tristan is having sex with a girl more than once."

"I bet you two thousand dollars that in one month's time, you couldn't get Rory Gilmore to sleep with you," Erik said.

Tristan smiled. "Easy," he said. "We can even shorten the bet if you'd like."

"Three weeks sound good to you?" Erik offered up.

In just three weeks, he would have an easy a thousand dollars. There was never a girl that said no to Tristan Dugray. He doubted that Rory Gilmore would be the first. He looked at Charlie and Michael. "Want to add some money to that?" he asked.

"I'll add a thousand," Charlie said without hesitation. It wasn't as much as Erik's offer, but he knew that Charlie was a little more cautious in losing his money since his parents weren't quite as loose with their money as Erik's and Tristan's parents were.

Michael was more hesitant. Tristan knew it was not because of money, though Michael didn't have much to offer up, but because he didn't know for sure whether or not Rory Gilmore could and would resist Tristan's so-called charms. He smiled, finally decided to go with his first intuition. "A thousand dollars," he said.

Tristan knew that was a stretch for Michael to offer up so he must've been pretty sure with his option.

"It's a deal," Tristan said. "And if Rory"—he stopped for a second and laughed—"if Rory doesn't, I'll owe you guys the four thousand."

"Each," Charlie added.

Tristan shook his head. There would be now way that he would be spending twelve thousand—not that he would have to.

"If you're so confident that you're going to win, why does it matter? Unless, you don't have total confidence…" Erik trailed off with a smirk, knowing how to get to Tristan.

"Yeah," Michael said. "Plus, if you lose a bet, you should have to do more than just pay us. There should be something extra…"

Tristan gave them a cocky grin. "Fine, twelve thou."

"You at least have to do something more than that if you lose," Charlie said. "Michael's right. The stakes aren't high enough. You are the betee here."

"I'm the what?" Tristan asked.

"The betee," Charlie repeated. "We're the beters and your the betee. So we are betting you four thousand dollars that we'll give to you if you win. But if you lose you have to…"

"Give us the twelve thou…" Erik continued.

"Run around in tighty whities with a monkey strapped to it?" Charlie suggested. When he earned questioning glances from the others, he offered a shrug. "What? Graduation isn't for another two years so we can't go _She's All That_."

"That's lame," Erik commented.

"You have to remain celibate for life," Michael offered up.

"That's just too cruel," Erik said with a laugh. "How about at least a month? If we're sticking with movie teams, we can go _40 Days and 40 Nights_ on him."

Michael shook his head. "Now this is just said. First, Charlie has seen _She's All That_ and now you've seen _40 Days and 40 Nights_."

Erik smirked. "What can I say? That Josh Hartnett is a hot-tay. And I don't blame Charlie. Freddie Prince Jr. and Paul Walker? Can we say a two-for-one deal?"

"Wow…watch chick flicks much?" Tristan asked.

"I _do_ have a girlfriend _and_ three sisters, thank you very much," Erik responded.

"Still…" Michael just shook his head, trailing off. "Is it a bet?" he asked.

Tristan nodded and reached out and shook hands with each of his friends.

As the conversation was brought back to the fact Erik knew chick flicks, he leaned back against the booth, his hands behind his head. This would be easy. All he had to do was make his first move.

---

Rory Gilmore sipped her coffee as she sat across from Paris Gellar, who had surprisingly become her best friend—at Yale and almost otherwise. Her mother still remained her best friend, as well, but, though Stars Hollow was nearby, Rory needed someone to talk to when she while she was at Yale within walking distance (in this case, she just turned to the next bed). It kept the phone bills down from Rory having to call her mother more than at least twice a day.

"Has Dean called yet today?" Paris asked.

Rory was still going out with Dean, her longtime sweetheart. He called at least once a day; he was still in Stars Hollow. It was hard, but they had kept their relationship together even though it had become a long-distance one. Plus, a 70-minute drive between Stars Hollow and Yale wasn't too bad.

Rory nodded. "He told me that he wants to talk to me about something really important and that it can't be done over the phone," she said with a shrug. "He's coming up tomorrow."

"He wants to talk to you about something important, huh?" Paris questioned. "You guys have been going out for four years now, think he may propose?"

Rory face lit up at the suggestion. Why hadn't she thought of that before? Of course he would propose. They had been together for around four years now, like Paris had said. Rory had contemplated breaking up with Dean the summer before their senior year due to feelings she'd developed for Luke's nephew, Jess Mariano, but after Rory's summer spent in Washington, Jess had hooked up with another girl, giving Rory a hard time when she came back. So, she gave Dean another chance, which she was happy that she had done so, as Jess had disappeared sometime during their senior year. They were, however, on okay terms when he left, as he'd long since broken up with his summer-girl, Shane.

"He's coming up tomorrow, you said?" Paris asked, interrupting Rory's thoughts.

"He is driving up here to see me tomorrow about mid-afternoon and then will drive back later at night," Rory said. She sucked out the last bit of her coffee through the straw and then started to get up. "I'm going to get another coffee to go and then why don't we leave? I feel like dancing right now."

"I'm not going to one of those clubs or a party," Paris said as she and Rory headed over to the counter. "My mom isn't her to force me to go to one."

Paris had changed since high school, but not with the social aspect. No parties for her.

"No, she's not here," Rory said, grinning. "But _I'm_ here to force you to go to one. Please? As a celebration for my soon-to-be engagement with Dean?"

"Why can't we just go to dinner somewhere with a few friends and call that a celebration?" Paris asked.

"Because I want to dance, not eat," Rory said. She wasn't really a party person either; she had only been to a few dances in her life. But right now she was in the mood to go to one.

Paris didn't answer because Rory had reached the front of the line. Rory ordered her coffee and then once she had received it, she and Paris left.

"Please, please, please?" Rory begged as they walked across the quad, back to their dorm.

"I have a test coming up in physics next week," Paris said. "I really need to study for it."

"I promise you that I'll help you study for that test starting tomorrow and everyday up until you take the test if you go to that party with me," Rory begged. "Please, please, _please_?"

"Fine, I'll go with you," Paris relented.

"Yay!" Rory exclaimed. She started skipping around.

"Rory, stop it!" Paris exclaimed, slightly embarrassed at her friend's antics.

"Sorry, I'm just so…excited! My best friend and I are going to go to a party _and_ I'm going to get married!" Rory exclaimed. "Nothing in the world could go wrong."

"I just felt a drip-drop," Paris said, looking up into the sky that was filled with gray clouds, nothing clear in sight. "Rory, whenever someone says that nothing could go wrong, something _always_ goes wrong."

It started to pour; the rain wasn't gentle and it hurt Rory's arms, as she was only wearing a light t-shirt, but she danced around in it, holding her arms above her head. Though she was getting drenched, nothing was going to get her down today.

* * *

Note: I don't own the movies that were mentioned…or anything else that may have slipped my mind at the moment. Also, I've never seen _40 Days 40 Nights_ so I don't know if it was quite a chick flick or not…but good enough for this chapter. 


	2. Getting Ready

_Author's note: Okay, it's been so long since I've updated. I'm extremely sorry to those of you that were waiting for the story, though I doubt there's any really. It was over a year ago that I first posted this story and I'm going to work hard to finish it before the year is up. I still remember most of the ideas I had as if it were yesterday that I started writing this story. I just haven't exactly had any inspiration to write it, but I promise you, I won't take almost two years for the next update._

**Can't Bet With Love**

Part Two:

As soon as Rory and Paris got back to their dorm room, Paris headed for the bathroom to shed her wet clothes and take a shower and Rory grabbed the phone to call her friend Mallory King, who lived in the same dorm as Rory and Paris. Rory and Paris shared a common room with Mallory and her roommate as well as two other girls. Normally Rory would just go to Mallory's room but she opted not to since she was dripping with water.

"Hello?" Mallory said after the third ring.

"Hey Mal, it's me, Rory," Rory cradled the phone with her shoulder as she grabbed a towel and dapped her hair with it. Luckily, her hair was cut short and so she wasn't too much of a drowned rat.

"Hey Rory. What's up?" Mallory asked.

"Nothing much," Rory responded. "Paris and I were just wondering if the invitation for tonight was still open."

"Of course it is!" Mallory exclaimed. "I just didn't expect you guys to take me up on it. What changed your mind?"

"Some pretty exciting news coming up," Rory told her with a grin. "I think Dean might be proposing!"

There was silence on the other line for a moment before Mallory responded, "That's great, sweetie! What happened to make you think this?"

"Well...called me today and asked if he could see me tomorrow. He's coming up here and he said he had to talk to me about something really important. I didn't see it at first, but Paris pointed it out and I don't know how I didn't see it before," Rory explained.

There was another moment of silence. "Wow. Are you sure? I mean, Rory, you don't want to be expecting something that may not even happen."

"Trust me," Rory said, "it will happen. Dean and I have been together since sophomore year of high school. Over the past year, we've discussed the idea of marriage. I didn't think it would happen until later on, but...who knows."

"Yeah, exactly, who knows? Rory, I just don't want you to get your hopes up," Mallory told her friend.

"I know, Mal," Rory said. "And I'm telling you I'm not getting my hopes up because it's going to happen."

"Okay," Mallory said. "Anyway, I can drive you and Paris if need be. I'll be leaving with Steph in about twenty minutes."

"I think we'll be needing a ride," Rory told her. "So we'll be over in fifteen."

"Okay," Mallory said. "See you then."

Rory hung up the phone then and crossed the room to knock on the bathroom door, where Paris was in the midst of taking a shower. "Paris?" Rory called out. "We're leaving in fifteen so hurry up. I'd like to be able to take a shower too."

Rory headed over to her closet where she picked a dress to wear. It was red and would end just above her knees. She hadn't had a chance to wear it yet because it wasn't exactly the thing you'd wear to class. Her mother had bought it for her a couple of months before.

Paris came out of the bathroom in her terry green bathroom and Rory headed in with the dress in hand. She took a quick shower and after drying herself off, she slipped into the dress. She blow-dried her hair before applying a little makeup onto her face. When she stepped out of the bathroom, Paris was already ready and was just going through her purse.

"Hey," Rory said. "We're meeting Mel in"- Rory paused and looked at the clock on her nightstand- "Well, right now."

"Okay," Paris said.

Rory slipped on a pair of shoes and grabbed her own purse before following Paris out of their dorm room and down the hall to Mallory's room. Rory passed Paris to knock on Mallory's door. Mallory's roommate, Steph, was the one that answered.

"Hey, come on in," Steph said, opening the door wider to let them in.

"Hey," Mallory muffled voice said. She was digging through the closet and Paris and I could only see her backside. "Found them!"

She came out with a pair of black heels. She stood up, coming to her full height of 5'10". Mallory was extremely beautiful Italian with curly dark brown hair and dark brown eyes to match. Several times she had been approached about modeling, but she had always declined the offer.

"I'm so glad you guys changed your mind and started to come," Mallory said as she slipped on her heels.

"Good thing Erik's so tall," Steph teased her. "Otherwise you sure would tower over him tonight. Those shoes make you at least 6'1"."

Mallory grinned. "I'm lucky to have fallen in love with a guy whose 6'3"." She turned and looked at Rory and Paris and her grin widened. "You guys finally get to meet Erik."

Rory nodded. She had met Mallory when school had started during a meeting for the floor in their dorm. Rory's grandmother had donated a large screen television along with a DVD player and surround sound and Rory had wanted to get rid of it, but everyone else had disagreed. It wasn't long after that that she became friends with Mallory, along with Paris, and even though Erik had been by the dorm many times, both Rory and Paris had yet to met him, though they had heard a lot about him.

"I like your dress Rory," Steph complemented her. "Is it new?"

"It was five months ago," Rory answered. "But this is the first time I've worn it."

"It looks great on you," Mallory agreed with Steph. "You'll have guys falling over you all night."

Rory blushed. "I doubt that, but thanks."

"I don't," Paris said.

"I like your dress too, Paris," Mallory said.

Paris didn't say anything, but Rory could tell she was pleased with the compliment.

"So am I driving or are you?" Steph asked.

"Do you know where Michael and Tristan live?" Mallory asked.

"No," Steph answered.

"Then I'll drive." Mallory grabbed her purse and took out her car keys from it.

"Michael and Tristan?" Rory asked.

"They're friends of Erik's as well as friends of mine."

"Tristan Dugrey?" Paris asked.

"Actually, yes," Mallory said. "Do you know him?"

"Since Kindergarten," Paris said. "I heard through my mother that he went here I just haven't had the 'pleasure,' of seeing him." Paris said the word pleasure with sarcasm.

"I'm guessing by that, your experience with Tristan wasn't very pleasuring," Mallory said.

"I had a crush on him and he barely knew I existed," Paris elaborated.

Steph smiled. "I don't know who hasn't liked Tristan at one point or another."

Mallory smiled. "In fact, you like him right now." Steph just smiled back at Mallory. "I, myself, have never had a crush on Tristan Dugrey. He's too self-assured for me. I'm more for the sweet a little less confident guys. I find it endearing."

"Now wonder you like Erik," Steph grinned. She turned to Rory and Paris. "He's just about the nicest guy you'll ever meet."

"I'm not so sure about that," Mallory said with a slight laugh. "But he does portray that image pretty well."

"He owns that image," Steph teased.

"So who is this Michael?" Paris asked. "I'm assuming he lives with Tristan since you said Tristan and Michael's."

"You assume correctly," Mallory said. "Michael Pratt. He and Tristan met at military school."

Paris nodded. "Never heard of him."

"I have," Rory said. "He's in my English class. He asked me out, actually."

Mallory smiled. "You probably wounded his ego when you said no. He and Tristan are alike in the self-reassured category. Charlie Richards, another friend of theirs, is pretty shy too. I'm not sure he could even ask a girl out. Normally, they have to come to him."

"I could see Paris going for a guy like that," Steph said. "Since she's so...forward."

"I think she would scare Charlie to death," Mallory responded. "No offense, Paris."

"None taken," Paris said. "I happen to have that effect on some people."

Rory laughed. "Tell me about it."

_Author's Note II: Yes, I know it's short, but this has been sitting around on my computer for a couple of months now. Originally Rory and Tristan's meeting would be in here as well, but due to the fact I hadn't finished that part yet I decided to cut it all out and just post this. Yes, I know it's a little boring, but hopefully it will get more exciting quickly. Thanks to all the reviewers and I'm sorry I didn't get this up sooner. I'm going to the ocean tomorrow so it will be at least a week before my next update._


	3. Party Hardy

**Can't Bet With Love**

Part Three:

"So, Mal," Rory started, "where's the infamous Erik?"

They'd just arrived at the party and Rory was starting to get a little nervous. She was wondering if this was the right idea after all. Could she still back out now? She and Paris could go out to dinner to celebrate instead…

Mallory scanned the room before her eyes finally landed her boyfriend. At the sight of him, Mallory grinned. He was a sight to see with his light blue eyes, his tousled brown hair, and body, tan and fit from spending time in the sun and at the gym. "Come on," Mallory said. "I'll introduce you guys to him."

"Is Tristan with him?" Stephanie asked, looking around the room.

"Yeah, why?" Mallory asked.

"I'll come," was all Stephanie said, offering no response towards Mallory's question. However, Mallory didn't need a response. She knew Stephanie's reason for asking. Mallory just smiled.

"Erik!" she called out as she was just a few feet away from him, Rory, Stephanie, and Paris trailing behind her.

Erik turned at the sound of his girlfriend's voice, a grin on his face. "Hey baby," he said. He put his arms around her and gave her a quick kiss on the lips. "You look nice," he whispered.

"Thanks," Mallory said. She slipped her hand into Erik's. "You know Steph"—Erik nodded—"but these are two of my other friends, Rory and Paris."

Erik's smiled at both of them, dimples intact. "Nice to meet the two of you." He gestured towards his three friends that gathered around him. "This is Charlie, Tristan, and Michael. This is Tristan and Michael's apartment so therefore it's their party."

Michael nudged Tristan before speaking. "Hey Rory," he casually said, not letting it be known that he had been affected when she had declined. "Nice to meet you, uh, Paris."

Tristan and Charlie said hi as well before Tristan was dragged off by Stephanie onto the dance floor. Rory could definitely see what they had meant earlier by calling Charlie shy. Tristan had given them a cocky smile that told other people that he knew he was hot. His smile was sort of a "come get me, you know you want me" sort of look.

Erik and Mallory left soon after without anything more than a "see you later." They headed of the opposite direction of where the crowd was. Rory looked a little confused as to where they are going.

Michael noticed Rory's confusion and grinned. The girl was so innocent it was endearing. Tristan had broken many girls like her before, but for some reason Rory seemed different than the rest of those girls. "They're going to my bedroom," he explained to her.

"Ooh." Rory nodded, now understanding why they had rushed off. Silence filled the air as she awkwardly stood there with Paris, Michael, and Charlie. "I'm going to go get myself a drink."

"I'll show where they are," Michael said.

"I don't think the kitchen would be that hard to find," Rory replied.

"They're out on the back deck," Michael said. He motioned for Rory to follow him, which she did. Paris and Charlie followed as well, not wanting to be left alone together.

The back slider that led out to the deck was open and Rory saw several cases of beer. She had originally been thinking of water, but she didn't decline when Michael handed her a can. She was celebrating after all. When Michael offered Paris one, she declined

"Oh come on," Rory said. "We're celebrating."

"What are you celebrating?" Charlie asked curiously.

"Rory's boyfriend is proposing," Paris answered.

Michael almost dropped his beer when he heard this. Tristan sure had his work cut out for him. Though he'd gone for and succeeded in wining over several girls that were engaged and even one who was married before, but with Rory, as Michael's mentioned before, it just seemed different. Michael wondered if for once Tristan Dugray would actually lose a bet.

----

"Hey," a voice said. The voice's owner had snuck up behind Rory, surprising her.

She turned around and the blonde guy… Tristan she thought his name was… was standing there, offering her an unopened can of beer. "Thanks," she said, accepting it.

Tristan's familiar smirk was on his face and he opened his mouth to say something. By the way he was looking at her, running his eyes up and down her body like she was a piece of meat, Rory had a sinking suspicion that he was about to hit on her.

"Sorry," Rory said. "I'm not interested, I have a fiancé."

Tristan's smirk didn't waver. "Then where's the ring?"

Shoot. "It's"—she started to say.

"Don't flatter yourself, Gilmore," Tristan said. "I never said I was interested."

Rory ignored his comment, everything he said except for her last name. "How'd you know my last name was Gilmore?" she asked. She didn't remember it being mentioned when Mallory had introduced her to all of them.

"Michael's mentioned you," Tristan said. "You shot him down. Smart."

"I'm a good judge of character," Rory said. She took a sip out of her drink before handing it back to Tristan. "Which is why I'm leaving now."

"Hey," Tristan started, but Rory ignored him.

Rory found Paris and headed over to her. "I'm ready to go," Rory told her.

"Praise the Lord!" Paris said, setting down her drink.

There was nobody to say goodbye to since Mallory and Erik still hadn't reappeared, Steph was on dancing with some guy Rory had never seen before, and both Michael and Charlie were out of sight. And Tristan… she wasn't even going to waste any more conversations with him.

Little did she know how wrong she was.

----

_Author's Note: Thanks to those of you that have reviewed for the first and second chapter: gilmorgal669, sleepneeded911, shadowgoddess1, SeleneA, lunatix988, fallenangel14 (I don't exactly like the idea of making a bet over Rory either, but it makes for a good story for me to write. Hopefully you'll be pleased with how it ends.), girldevil, bonebaby, mischa, katie, smile1, laura, kiki, mar0506 (keep in mind that Tristan has no clue that Rory is going out with Dean. And a little boring? Ha, you're being nice. It's was a LOT boring!), Callista NicTeryn, catherine (thanks :) as for whether or not Dean will propose…well, you'll find that out in the next chapter), aurabell, and omarion. I hope this chapter was more exciting then the last chapter!_

_ I'm not at all getting the characters personality's right. Sure, I still watch Gilmore Girls (and I will tell you how disappointed I am with Rory sleeping with Dean—especially when he's married—but also because she's supposed to be with Tristan. Or Jess—I'm a fan of his as well.) but I've kind of veered away from being a huge fan and sadly I don't know the characters all the well. Oh and for the sake of my story, Rory never slept with Dean so she's still a virgin._

_ I also am only a high school junior so that makes me sixteen-years-old. I've never been to a college party so I have no clue what it would look like so sorry that I'm not exactly descriptive in this chapter. And I know my dialogue sucks. For some reason I'm really stuck on things to say… and ideas with this story. So if you have any, they would be welcome._


	4. A Date With Destiny, or not

**Can't Bet With Love**

Part Four:

Rory sat in the common room that she and Paris shared with four other girls, Mallory and Steph included. The large screen television that her grandmother had donated was turned to the news, but at that moment, Rory's mind was elsewhere.

"Hey, whatcha watchin'?" Mallory bounced onto the couch next to Rory.

Rory turned to her friend. The brunette wore an oversized t-shirt that she assumed was her boyfriend's and a pair of dark blue shorts that barely showed with the long t-shirt.

"News," Rory told her.

Mallory sat down next to her. "How boring," she commented. She reached her hand out for the remote. "You mind?" she asked.

Rory shook her head, handing Mallory the remote. Mallory started to flip through the channels before landing on MTV.

"Everything alright?" Mallory asked, looking at her friend with concern.

Rory nodded. "I'm just a bit nervous. Dean called and he'll be here at five. We're meeting for coffee."

"How'd he sound? Excited, nervous…?"

Rory tilted her head to the side. "What does it matter?" she asked.

"Well…if he's excited, it could mean that he just has some good news to tell you…now if he's nervous…" Mallory trailed off. Tilting her head like Rory had, she asked, "Do you get what I'm saying?"

Rory nodded. Thinking back to her conversation with Dean, she decided, "He most definitely sounded nervous."

Mallory examined Rory's face, trying to decipher what her friend may be feeling. She didn't want Rory to get her hopes up. She'd never met Dean, but he had loyally called Rory at least twice a day. There was no doubt that he was smitten with Rory, but Mallory still wasn't quite sure if a proposal would be happening today.

Giving up on guessing, Mallory asked, "If he asked you, what would you say?"

"I think I'd say yes."

"So, Dean's it?"

"Yes, I think he is."

"Are you _sure_?"

"What's with all these questions, Mal?" Rory asked, now irritated. "Yes I'm sure; I _love_ Dean—why wouldn't I say yes?"

"I just want you to be sure that you're making the right decision, that's all," Mallory responded.

There was silence as Mallory continued to watch MTV and Rory grabbed her notebook sitting on the coffee table and begun to complete her journalism assignment. Around 4:15, Mallory shut off the television and turned to Rory.

"Look, Rory—I'm sorry for questioning you. I know you love Dean, and I know he loves you. You're nineteen; I just don't want you to rush into anything."

Rory raised an eyebrow. "Have you ever known me, of all people, to rush?"

Mallory shook her head. Standing up, she motioned for Rory to follow her into her bedroom. "Come on. You need an outfit tonight so hot that he won't be able to resist you."

Rory smiled and let Mallory lead her into her room.

About half an hour later, Rory appeared again, dressed casual with a glamorous touch, thanks to Mal, who pieced together an outfit using items of Rory, Mal, and even Steph, who was wasn't there to have a say, but Mallory reassured Rory that it was alright.

"Gorgeous, dah-ling," Mallory purred.

Rory smiled. "Thanks." Then, she checked her watch. It was 4:45. "In these heels, if I want to get there in time, I better leave now."

"Bye now," Mallory said with a wave.

Just as Rory left, the phone rang.

Mallory picked it up in her usual fashion. "Hello, _gorgeous_ Mallory here. What can I _do_ for you?"

"Hey babe," Erik said. "Let's get together and we can discuss what you can _do_ for me."

"No thanks," Mallory teased. "I was expecting someone else to call."

"What, you got another boyfriend hidden away?"

"Hidden, no," Mallory shook her head, though Erik wasn't able to see her. "_You're _the one who's hidden. I just think you look good."

"_Sure_," Erik said. "I know I'm cuter than any other boy you could find."

"Please, Erik," Mallory rolled her eyes, although Erik couldn't see her, but her tone conveyed her actions. "Who ever said I wanted a just a '_cute_' guy?"

"I'm hurt," Erik feigned. Then, changing the subject, he said, "Let's go get some coffee."

"No, not good," Mallory said. "Rory's going there with her boyfriend—possible proposal here—she might think I'm spying on her."

Erik was silent for a minute. "So it's that serious, huh?"

"Could be," Mallory said. "I've never met the guy, although he _does_ call up here at least twice a day."

"I'd like to see this guy," Erik said. "I'll swing by there and pick you up in five?"

"_Erik_," Mallory tried to reason. When he wouldn't back down, finally, she relented. "Fine, but make it ten."

As Mallory ran into her bedroom to get ready, she wondered how Rory was doing.

----

"So does this place compete with Luke's?" Dean asked as the two stood in line.

Rory shook her head. "Nothing comes close to Luke's."

They ordered their coffee and sat down to wait for them. Dean seemed to fidget nervously. Rory just wanted to tell him to "spill it out, already."

"Well?" she prompted.

"I"—Dean stopped when he saw the coffee coming. He looked relieved; Rory just sighed.

She took a sip before looking up at Dean expectantly.

"How's school been going?" he asked.

"Schools been well," Rory answered.

"Liking all your professors?"

Rory nodded. On any normal afternoon, this would have worked distracting Rory. She could have talked about her courses or really good professors that she lucked in getting. But not this afternoon, not now.

"Paris doing alright? Still as crazy as ever?"

Rory contemplated this for a moment. "Paris is still…Paris."

"How about you're other roommates? What were their names again?"

Rory sighed. "Mallory and Stephanie; they're fine. And before you ask, yes, my mom is fine, so are my grandparents, my car, and _even_ my television is in fine working order."

Dean looked mildly amused. Looking up at the door, he nodded his head towards it. "That group seems to know you."

Rory turned around, spotting Mallory who sheepishly waved in Rory's direction after she saw that Rory had spotted her. With Mallory was her boyfriend, Erik, and two of Erik's friends; Michael and Charlie. The fourth one, Tristan Dugray, who Rory hadn't taken a liking to, was a no show. She couldn't help but be thankful for that one.

"Want to invite them to join us?" Dean asked. Before Rory could protest, he motioned them to come over.

Mallory tried to protest, but Erik was already dragging her towards Rory and Dean.

Erik held out his hand to Dean. "I'm Erik."

"Friend of yours, Rory?" Dean asked, not recognizing the game.

"You could say that," Erik said.

"Dean, this is Mallory, one of my other roommates. Erik's her boyfriend and these are his two friends, Michael and Charlie. Michael's also in my journalism class."

Dean raised an eyebrow. "The one that persistently asked you out?"

"Glad to make a name for myself," Michael offered him a smile. "If it's any constellation, I didn't know she had a boyfriend until last night, at the party."

The amusement from Dean's face faded. "Party?"

"It's not like I went out with him or anything, Dean. Plus, I was at the party for what, five minutes, Mal?"

Jealous much, Mallory thought, but nodded. "I drove them there, but they left before I got a chance to see them again and took a cab back to the dorms."

Dean just nodded.

"Look, its Tristan," Charlie said, an amused smile on his face, one that mirrored in both Erik's and Michael's.

Mallory recognized it, grimaced, and said, "Oh no."

* * *

**Author's note**

----

Eek—I'm so sorry about how long this took. I wrote this chapter out on paper and actually liked it, but lost it, and I just was frustrated and started this. It's different than before and not too sure I like it, but if I held on anymore it would be October before I updated. I have a good idea of what's to happen in the next couple of chapters so updates should be more frequent. I'd say the next chapter will be up no sooner than two weeks from now. I'm going out of town, but maybe I'll squeeze one in before then. Thanks for all your reviews, I really appreciate them!

_Thanks to:_

**Callista Wolfwood**– Thanks for the suggestion. That's what I _want_ to happen, but I have a little problem writing from the point of view of characters that I didn't create. I'm trying to work on that… so hopefully something actually _interesting_ will appear soon. Thanks for reviewing!

**MegLiz716**– Hmm… it's not over yet so you'll see what happens in the next chapter :) I'm glad you like it! Thanks for the review.

**Indieemo-gurl21**– I'm glad you didn't like it. You'll find out whether Dean proposed or not in the next chapter. It was meant to be done in this one, but there was a scene I wanted written in between, but I didn't know how to go about doing it so it's being pushed back. Thanks for reviewing!

**TRORY**– Thanks for the review. I'm continuing…just a little slow at it.

**Paige**– Thanks for the review. Sorry the update was so long. ;)

**Liz3386**– I'm glad you like the little details like that. There aren't that many of them in there. Thanks for reviewing!

**Smile1**– I shouldn't tear my story down, yes, but… I think its lacking a lot of things that it could use. Originality is one of them. I started this story over two years ago and when I went to reread it, I didn't like it at all, but I decided to give it a try because it would be a challenge. I'm glad you like the way I write them… because I know I'm not getting them right at all. I understand what you mean about Tristan and Rory… I'm glad you could see that. I know I was vague and it was really hard to submit because normally I'm a description whore. The past two chapters have really irritated me because they've been lacking in what I'm normally writing a lot about. The dialogue could use _a lot_ of work. I think I just worry too much about making them out of character that I freak out and it just turns out not good. So maybe I should try and relax about it a little more. Thanks for the review and all your comments. They've helped me out so thank you.

**Amanda**– Thanks! I will keep writing… thanks for the review! And I have to finish this story first before I consider a sequel. ;)

**Four51**– Thanks… Thanks for the piece of advice… I'll try and work better on that. I have a pretty large screen so when I write it's not very big… so I'm sorry if it comes up that way on yours. I'll try and work on that better. Thanks again for reviewing and the advice!

**Beauty unfolds**– Thanks for saying it's a great story. I know the plot's overused. I started this a couple years ago… I think it had a mix to do with watching She's All That, but I came up with the idea and I know it's horribly unoriginal and I almost deleted it, but I'm trying to better my writing talent and writing this is a real challenge for me. Coming up with ideas are easy, but writing someone else's character is a lot harder. I tried to get Rory's actual personality because I know that wasn't how Rory acts, but… my fingers typed out a new one. Thanks for the idea… I think I might use it.

**--------**– Sorry it took so long to post this chapter. I wrote one out on paper and then lost it, but I was too lazy to rewrite one, but here I am now. Next update should be quicker because I found my notebook for ideas of this.

**Mar0506**– Ugh… let's not even get me started on Dean. I've had it in for that boy since Day One. Okay not quite…I actually liked him when I re-watched season 1 still nothing beats Tristan.

**JALNA**– No, Rory probably never will understand him. I don't understand him and here I am, deciding to WRITE him. This is why you'll see very few from Tristan's point of view. Thanks for your review; your spiel spurted of some ideas.

Thanks for reading and please review! Feel free to plug your own stories and other good Gilmore Girls stories too. I've been out of the scene so I only keep up with what's in my profile, which isn't much.


	5. Once a Disaster, Always a Disaster

**Once a Disaster, Always a Disaster**

Tristan Dugray's appearance spread excitement through Erik, Michael, and Charlie.

Rory had no desire to see him again. Their encounter had been short, but when she was near him, she always felt like she was on display.

Mallory had witnessed her boyfriend and his friend's antics before—and she did not want them to be repeated on Rory Gilmore. Erik had let it slip the night before that they'd made a bet that Tristan couldn't get a girl and Mallory had found it amusing—the idea of Tristan Dugray failing since it was nearly impossible—until now when she was ninety-nine percent sure Rory was it's victim.

Sending a glare Erik's way, she felt like she had feed Rory to these boys. She was ashamed to say her boyfriend was one of them.

Mallory leaned over and whispered in Erik's ear, quietly so no one else could hear, "You warn Tristan not to mess with Rory and her boyfriend or you can forget about me _doing_ anything from me."

Erik's eyes widened at Mallory's threat. He stood up and headed over to the counter, dragging Mallory along with him. "Mal," he whispered. "Tristan could actually _lose_ this one."

"Find another girl; stay away from Rory Gilmore."

"Mal…" Erik whined.

"We'll discuss this later," she whispered back. Nodding her head towards Tristan, she said, "Now go call off the hound dog and let's get out of here."

"Mallory, the guys are going to make fun of me so much if I call this off because _you_ told me to. They say I'm whipped enough as it is."

Mallory gave him a small smile. "Show them how whipped you really are by calling this whole thing off."

Erik sighed and walked over to meet Tristan.

At the look on Erik's face, Tristan raised an eyebrow. "What's the problem, buddy?"

"Mallory knows about the bet and apparently, our love life—if you know what I mean—depends on whether or not this is carried out. How 'bout"—

Tristan shook his head. "No, we already agreed. No backing out of the bets."

"Tristan, this has _nothing _to do with being afraid that I'll lose the bet. I'm confident that we'd win. This has to do with my love life—or lack there of after you're finished with irritating Rory and her boyfriend."

"I had no such plans," Tristan said. "Just like I have no plans in stopping this bet. Just tell Mal that it's out of your hands now."

Erik shook his head. "She's not going to accept that."

Tristan shrugged, not caring about Erik's predicament. "Too bad, but forfeiting this bet is your only option, meaning you'll have to pay up…and complete actions that Michael, Charlie, and I will have to discuss. By wimping out" —

"I am _not_ wimping out," Erik interrupted. "The bets still on—Mal will just have to learn to deal with it."

Tristan smirked. He left Erik, heading to the table. Erik followed, scowling, knowing that Tristan just worked him to agree into the bet once again. Forfeit and wimp were not a part of Erik's vocabulary.

The encounter between Dean and Tristan didn't go over too smoothly.

"Is this Rory's infamous fiancé that I've heard so much about?"

Dean looked confused, but before he could comment, Rory interrupted, scowling for letting it slip out the night before that Dean was her fiancé _before_ he proposed.

_Note to self: when you make up lies, make sure the one you lied to doesn't meet the one you lied about._

Of course, since Dean would be proposing before the night was over, she wouldn't have to worry about having to lie about it any longer.

"His name's Dean. Dean, this is…excuse me, but what's your name again? Dustin?"

Tristan smirked. "Like you could forget; it's Tristan."

"What the hell kind of name is that?" Dean asked.

"I was thinking the same about yours," Tristan said.

"Wow…look at the time," Mallory pretended to look at the non-existent watch on her wrist. "It was nice to meet you Dean and I'll see you back at the dorms, Rory, but we must be going."

She took a hold of Erik with one hand and Tristan with the other. At request, Michael and Charlie dutifully walked out with them after they all shared a chorus of goodbyes.

Dean turned to Rory, one eyebrow raised, "You have an interesting group of friends, Rory."

Rory just smiled weakly, not bothering to point out that they weren't quite her friends—especially Tristan.

It was silent for a minute before Rory asked, "So, what'd you want to talk to me about?"

Dean paused for a minute, as he seemed to try and put words together.

_Here it comes_, Rory thought.

"You've heard me talk about my Uncle Speed, haven't you?" Dean asked.

Rory shook her head, confused. "You have an uncle named _Speed_?"

"Its nickname," Dean clarified. "He races cars—after he fixes them up."

Rory nodded, wondering why this was relevant to his news. "And…?" she prompted.

"And…he's offered me a job. In Chicago." He paused for a moment, studying Rory's face to see if he could decipher her reaction. "I've accepted the offer. I'm leaving in less than a month."

"What…but…what?" Rory started to sputter.

"I'm leaving, Rory."

"I got that part," Rory snapped.

Dean ignored her and continued on, "Stars Hollow to Yale is one thing, Rory, but from Yale to Chicago? It's almost 900 miles away."

"So are you…breaking up with me?"

Dean shook his head. "No, I'm not. If you would let me finish…" Dean trailed off. Rory didn't say anything this time so Dean continued on, "I'd like you to come with me."

"Come with you? To Chicago? _Now_? **_WHY_**?"

Dean nodded. "We go well together, Rory; like peanut butter and jelly."

Rory ignored his comment for the time being as she continued on her rant, "But…my mom…school…"

"Your mother can visit us; after all, she visits you here. And there's college in Chicago to," Dean tried to reassure her.

"Have you gone crazy, Dean?" Rory asked. "As you've said, Chicago is about 900 miles away. Stars Hollow is close enough where my mom and I can meet and spend the day together, but still go back to our respective homes. And school? I'm not leaving Yale to go to what…I don't even _know_ of a college in Chicago."

Dean was silent. It dawned on Rory then that he'd just asked her along—no proposal or even a _hint_ of a proposal. He'd just said that they went "well" together; like peanut butter and jelly. He expected her to move with him to a foreign city (to her, at least) and go to a school mediocre to Yale, live almost 900 miles away from her mother…and for _what_? Because they went "well" together and that peanut butter couldn't be away from jelly? News flash! Peanut butter _can_ be eaten without the jelly.

"What would I be along as?" Rory couldn't help but ask. "Support? Jelly?"

"My girlfriend, of course," Dean answered.

"Dean, we've been going out for a long time now."

"Yes, which is why I think we're reading to take this big step."

Big step? Moving to the same city? It _was_ a big step—especially with no proposal and the fact that they hadn't even slept together yet.

"I…just…I…I don't know, Dean. This is a lot to think about. I just…don't know."

"You don't know? Dean asked. "Either you do, or you don't."

Boy did those words sound familiar.

"Dean, this isn't about fear this time." Okay, maybe a little—fear of going insane if she agrees with it! "This is about moving to a foreign city where you're the only person I know. I'd be leaving behind…everything. My _whole_ life is here."

"I wouldn't be," Dean pointed out.

"I'm nineteen! I just can't go off gallivanting to Chicago because _you_ got a job. What about _your_ college?"

"Stars Hollow C.C. can transfer the credits."

The way Dean said it, Rory wasn't even sure that Dean would be showing up at a college in Chicago.

She wanted to tell Dean that she couldn't go—she just _couldn't_. But she loved him and he seemed to give an ultimatum—come with we or we're through. She couldn't believe that she was willing to _marry_ him this morning, but moving to Chicago was…impossible. Was she willing to give him up?

Dean sighed. "I'm sorry; I shouldn't have expected an answer tonight. I'll let you talk to your mom…make one of your pro-con lists…and then you can get back to me; alright?"

Rory nodded. "Okay."

"I'm still free to hang out tonight, if you want to," Dean offered.

Rory nodded once again. "Alright, what would you like to do?"

Dean shrugged. "Is there a movie theater around here?"

Rory nodded. "They're playing Rosemary's Baby tonight."

"Our first conversation," he remembered.

Rory smiled, "I was so nervous. You told me that you were watching me in a non-creepy way and I was telling you about the round cakes."

Dean laughed. He started to lead Rory to his car, but she shook her head.

"Let's walk—it's not too far from here."

Dean nodded, taking Rory's hand in his as she began to lead him.

Throughout the walk, they reminisced about their past. They'd gone since Rory's sophomore year—minus the few months they'd been apart due to the fact Rory hadn't been able to say "I love you" to Dean—so there were a lot of good memories to look over. Rory fingered the bracelet she wore on her wrist, the one Dean had given to her on her sixteen birthday. He'd been her first boyfriend, the first "I love you" outside of her mother. To Rory, it felt like it was closure; like Dean knew Rory wouldn't be able to leave this life behind to create a new one.

---

Mallory came home later that night, around eleven, and found Rory in front of the television watching a Meg Ryan chick flick that should never be viewed and was swallowing a large tub of ice cream.

Mallory raised an eyebrow, asking a question without the words.

"I think we just broke up," Rory answered the silent question. Tears formed around Rory's pretty blue eyes and Mallory sat down next to her to comfort her, rubbing her back reassuringly, as Rory poured out the story.

**

* * *

Author's Note**

This was supposed to be broken into two chapters—one of Tristan meeting Dean and the next of the news—but I had a hard time writing the meeting between Dean and Tristan to where it would be long enough for an actual chapter. I'm not too big of a fan on conflict…so writing it just doesn't go over too well. So I just wrote it roughly otherwise it would take longer out to get this…and I didn't want to make it months of waiting again.

Also, I'm considering rewriting the first chapter. It was written first when I was about thirteen (I'm now seventeen) and I cringe every time I glance at it.

Oh and if you live in Chicago…I'm sure there's good colleges there so don't be offended by Rory's thinking. I tried to research on a few colleges there that Rory and Dean could discuss, but I didn't get too far in my research. Rory would probably know, but unfortunately…I don't know.

I hate to say this, but the next update might not be so soon, as I'm stumped on where to go from here. Suggestions would be welcome if you have any ideas…I'll try to be as quick as possible.

**Review replies:** (sorry I can't do everyone, but I don't have the time right now)

**vm1fan225**: I know; I'm terrible at updating. But just to be correct, it's been 4 chapters in a span of almost three years—which still, not so good, but I mostly work on original stories so this isn't a top priority to me. I'm working on updating more and they _should_ be more frequent.

**Smile1**: Mallory's definitely different from Rory and I think by adding her in, it mellows Rory out a bit. I'm glad you think Rory was in character the last chapter and I hope to continue on that path. Rory deserves her own group of friends. In my opinion, she's such a likeable girl; it's unlikely for a girl like her to _not_ have friends. Paris was originally supposed to be her only friend at Yale, but I wanted a way to get them to go to the party so Mallory became Rory's friend, but not too good of a friend. I think that's definitely changing, though. Thanks for thinking that I'm creative. :) And I HATE jealous Dean. I was re-watching season 1 via the DVDS and I liked him _soooo_ much before he became all jealous. Still not a Dean fan, but he'd tolerable if he's not so jealous. So…hopefully in my story, he's tolerable. He'll be in the story more…whether he continues to be Rory's boyfriend or not.

**Thanks for reviewing: **Trory Lover, Courtney, omeomy, blazergrl17, nancerz-, KarahBella, Lauren, Princetongirl, Robin2, tickle582, cosmopolitan, tristian'jess'loganluver.

Thanks for reading and please review!


	6. Yale Has a Library?

**Can't Bet With Love**

Part Six:

Spectrum was the club a couple blocks away from Yale, one that most college kids attended often because it was easy to get in for those underage and the beer was cheap. It was two floors; the bottom floor had a large stage for band to play, followed by a large dance floor. The bar lined the right side of the club, and several tables lined the outside of the dance floor. The top floor had several booths—like those you'd get your picture taken in at the mall—with cloth covers that you could pull back so no one could see inside the booth.

That was Tristan's spot.

Every weekend—and sometimes during the week—he'd come and have a bit to drink before meeting a random and meet willing girl—sometimes the girls would know him, but he didn't have a clue of who they were—on the dance floor and head to the top floor with her.

Tonight's victim was a petite blonde. Tristan had met her at the bar, charmed her, and then promptly escorted her up the stairs.

Currently, she was sitting on his lap, her mouth open and tongue intertwined with his. He had his hands under her shirt, gently resting on her hipbones. Just as he was about to lift her shirt off, he felt a vibrating in his behind. He tried to ignore it, but when it rung again, he pulled away.

Reaching into his back pocket, he pulled out his small, silver flip-phone. Erik's name lit up the screen.

"Can you excuse me for a moment?" Tristan asked.

The girl—whose name he'd long since forgotten—stared at him incredulously, but stepped out of the booth.

Tristan flipped his phone open, pressing it to his ear. "What?" he demanded.

"Where are you at?" Erik asked him.

"Spectrum," Tristan answered.

"Ahh," Erik replied. "I'm guessing there's a girl waiting for you…"

"You guessed correctly," Tristan said shortly.

"I must ask," Erik paused for a moment, "if you're going to keep messing around with other girls, how do you suppose you'll ever get Rory? Great game plan, Trist."

Tristan scowled. "It's only day three of the bet," he replied.

"Three days down, only eighteen left to go…for a girl who's supposedly engaged, that's not a lot of time."

"What do you mean 'supposedly engaged'?" Tristan asked.

Erik ignored him, "Mal told me that Rory's at the library tonight."

"Shouldn't you be keeping this hidden from me?"

"With this girl…you'll need all the help you can get and then some. I know that's a bit difficult for you considering most of the girls you date…or just 'see'…are rather easy."

Tristan scoffed. "What, you don't think I could ever last with a girl?"

"No, I don't," Erik answered honestly. "Mal and I have been together for a year now. The day Tristan Dugray has a relationship that lasts a year…that's the day the world will end."

Tristan was quiet. He didn't know why Erik's words got to him. He liked living the single life. He liked having the freedom of being able to go to Spectrum whenever he wanted and hooking up with random girls. So how come, after hanging up the phone with Erik, the last thing he wanted to do was continue where he left off with the girl who was most likely waiting outside from him?

Tristan slipped out of the booth. "Sorry, but I've got to go."

The blonde looked a little frustrated, but stood on her tip toes, giving him a kiss. Reaching into her purse, she pulled out a piece of scratch paper and quickly wrote on it. Handing him the paper, she flashed him a brilliant smile before he moved on.

Looking down at the paper, he saw that she'd written her name and phone number.

He put it in his pocket as he made his way down the stairs and through the club, making his way out into the cold, October night. He quickened his pace to reach his car—a shiny black sports car—and once inside, he started it and accelerated back towards the school.

He'd make a stop at the library, he decided. The only problem was…Tristan didn't exactly know where the library was.

Pulling out a cell phone, he dialed Michael's number. Michael was the only person he could think of to know where the library was.

Michael answered his phone on the second ring groggily, "Hello?"

"Michael, have you been sleeping?"

"Tristan…whatever you need…this can wait until tomorrow."

Tristan had no doubt that his friend was sleeping. "It's ten…on Saturday night, no less. Get out…party…anything."

"I worked from six to nine…I think I deserve some rest," Michael responded.

There was a big difference between Michael and Tristan, although they were roommates and best friends. Michael was more serious, studious, and although he had dates, they no where neared the amount of Tristan's. Both of them came from rich families, but Michael, though he received money from his parents each month, still worked through the week and during a majority of the weekends.

"So what did you need? I know you didn't call me just because you were wondering if I was sleeping or not."

"Where's the library?"

Michael was silent for moment before he started to laugh. "Is this a joke? Tristan Jalen Dugray can't _actually_ be asking me where the library is."

Tristan rolled his eyes. "Michael, I have no time for games. Where is the library?"

Michael stopped laughing when he realized that his friend was serious. "Swing by the apartment and pick me up. I'll show you from there. I have to see you in a library to actually believe you went."

"Hahaha," Tristan said dryly. "I'll be there in five."

---

"Tell me why we're at the library again?" Michael asked as they walked into Yale's large library.

"Rory's here," Tristan said. "This bet doesn't last long—two weeks and five days from now—so I have to work fast."

"You don't just have to work fast," Michael commented. "You need a miracle."

Tristan scowled. "What I need is a little word of encouragement."

Michael just grinned. Never before had he seen Tristan so weary over a bet.

Tristan looked around the main entrance library. "Holy damn—this place is huge. How are we ever going to find her in here?"

"Oh ye of little faith," Michael drawled. "You'll find her."

"You're not going to help me?" Tristan asked. "What if I get lost?"

Michael laughed. "It's not that big, Trist."

He made his way over to an empty table, setting his book bag on top. It occurred to Tristan suddenly what exactly his friend planned on doing this Saturday night.

"I can't believe I'm friends with such a nerd that would consider studying on a Saturday night. I didn't even have to drag you here…you went willingly." Tristan considered it for a minute. "No, you _volunteered_ to come."

Michael just shook his head. "I'm going to go pull up some material for my English essay; go find your latest target."

Tristan just shook his head before heading on his way. He passed section through section; marveled at how large the library. He considered it to be a waste. Making his way upstairs, he made his way through each section, thinking about giving up, when he spotted her.

Tristan became aware of how pretty she was. She wasn't the normal girl he went after (though it wasn't by choice). She didn't have the suggestive clothes or makeup caked on. Instead, dark, chestnut brown hair was pulled back in a no-nonsense ponytail; wide, blue eyes focused on the paper in front of her; a slim, slender body covered in a light blue cotton sweater and a pair of fitted Levi's.

He approached her.

---

The section in the library Rory was sitting in was empty. Actually, aside from the one worker she'd spotted earlier, the whole library was empty. Everyone else had a better thing to do on a Saturday night than hang around with a stack of books. Rory, however, took advantage of this time to allow her to get started on her current English essay—a thirty-page piece, this time.

It was due next week, though it had been just assigned yesterday, so Rory was busy at work. Plus, when she kept busy, she hardly thought about Dean at all.

Yes, in fact, two minutes had passed since she last thought of Dean.

Rory sighed, trying to focus on her book. She had a piece of paper next to her, a quarter of the page filled with notes. Beside her, several other sheets sat, fully written on.

She also had a stack of information that she'd printed it off the internet earlier in her dorm. She'd already taken the time to sort through the papers, highlighted all the good stuff, and then formulated an outline and separated the info according to that outline, using sticky notes.

She'd been in the library since six o'clock that night and her patience was starting to wear thin. She had begun to wish that she'd taken Mallory up on her offer of going out for the night, as Mallory had claimed that was exactly what the doctor had ordered.

Instead, Rory sat in the library…her phone off incase her mother called. She felt foolish, thinking Dean would propose now, and hated to tell Lorelai the latest on Dean, although she had never let it slip she thought he'd propose. She knew her mother would ask too, as Lorelai had talked to the grandparents to get her out of one of the never-ending Friday night dinners.

Sighing, she took a highlight, different color than before, and begin to highlight key facts in the notes she'd taken. The highlighter didn't seem to work all that well so she pressed down harder.

Sighing, she'd always welcome any sort of break at the moment.

"You're really wearing out the highlighter, huh," a familiar voice remarked.

Rory looked up, a scowl come onto her face as she saw who had spoken.

She took back her previous thought.

---

**Author's Note:**

I was having a hard time with coming up with this chapter…so I decided to show in a little more detail about Tristan's life. It's choppy and I didn't get a chance to edit it because I'm on the way out…so tell me if you see something and I'll make the changes that need to be made and repost it.

I don't think I've mentioned the date/month before…so I've decided that it's about October. I think when I originally started writing this, it was supposed to be set about the spring of freshman year…but it's going to be sophomore year instead. I'll reread the first couple of chapters soon and edit them as to fit with this.

Oh—and I know nothing about Yale and I was too lazy to see if there was a map of the campus online so details are pretty vague when it comes to Yale's campus. The library is just based on, well, other libraries.

I rewrote chapter one so make sure you go back and check it out. Not too many changes, but edit/add to other chapters so…I'd check it out if I were you.

I hope to get chapter seven up soon, but it's my senior year in high school and I have a job now…so the next review might take a while. Sorry guys…I'll try to update as soon as I can.

**Thanks for the reviews:** Tristian'jess'logan'luver, Princetongirl (for the two reviews), LoVe23, jalna, nancerz-, emmy, tickle582 (yes, it's a trory. It's slow…but we'll get there eventually.), eternalgorithm, and jen.

_--If you read all of this, put a star at the end of the review…just so I can see who actually reads my notes--_


	7. Rejection Hurts

Part 7:

"You're really wearing out the highlighter, huh," Tristan commented as he approached Rory. He saw her glancing in his direction, a scowl marring her otherwise angelic face. A smirk grew on his mouth, "You know, if you hold that face long enough, it may stick."

Rory's scowl grew. Ignoring his comment, she said, "So what are you doing in Yale's library? Took a wrong turn while traveling to Spectrum?"

Tristan wanted to correct her that he'd come _from_ Spectrum, but he knew he needed to get working if he wanted to win Rory over. "You know, some of us _actually_ study," he told her.

Rory raised an eyebrow. "Oh?" She gestured towards his empty hands. "Then where is your book bag? No paper, pencils, nothing?"

Tristan didn't think about that one. Luckily, he was quick to come up with something that sounded good. "I'm looking for…this book," he reached out and pulled the nearest book to him. "My book bag is in another section."

Rory smirked at the book title. "Interesting…and what class is this for?"

Tristan looked down, spotting in large print "Pregnancy for Dummies." He scowled. "It's not for a class…it's just research."

"Oh? Did you happen to get a girl pregnant?"

"No, no, nothing like that," Tristan said. And it was the truth. Although Tristan had several sexual partners, he was always sure to take precautionary measures to prevent anything like that from happen. "My sister's pregnant." And that…it was a lie. "I told her I'd pick something up for her."

Rory nodded. "How far along is she?"

"Twenty-two…weeks," Tristan fibbed.

"Must be real…" Rory paused for a moment to find the word, "…exciting for your family."

"Yeah, we're pretty excited."

Rory just nodded once again, looking back down at her notes. When she realized Tristan was still standing there, she looked up with a scowl on her face. "Don't you have some place to be?"

Tristan shook his head, pulling the chair out and sitting across from her. "I think I'll just stay here and absorb this book for a minute, that way I can make sure it's alright for Natalia."

Rory watched as Tristan cleared his throat and opened the book, his crystal blue eyes scanning over the page. She sighed. She knew guys like Tristan before, they were ones that when you pushed, they just pushed back harder. She tried to take another tactic and ignore him. That way he'd get bored and would go away.

She started reading her notes once again, trying to use the worn out highlighter. Letting out another sigh when the highlighter refused to work, she put the cap back down and tossed it near the bright yellow one. Digging through her leather messenger bag, she hoped to find another one, as she had a vast collection of them in all sorts of colors, but her search came back empty.

Tristan cleared his throat, something that began to grate on Rory's nerves. When she glanced up at him, he seemed entirely focused on the book he was reading. His eyebrows were even furrowed, as if he were trying hard to concentrate, something that was impossible now for Rory.

Maybe she could still contact Mallory; it wasn't _too_ late, after all. The last thing Rory needed was to spend the rest of her night busying herself to rid the thoughts of Dean when they only lead her to think even more about him.

The highlighters had been a gift from Dean. She'd discovered a note that Dean had slipped into her textbook when she wasn't looking, something she'd seen for the first time tonight. She didn't bother to open the envelope once she recognized his unusually neat handwriting, for a guy at least. Even Tristan, in a small way, reminded her of Dean. He was there that night, after all.

After tossing her textbooks into the bag, Rory began to organize her notes before putting them into her binder and putting that into the messenger bag as well. Standing up, she grabbed the bag, swinging it over her shoulder and collected the textbooks that she'd taken inside the library itself.

"Where are you going?" Tristan asked, standing up, library book in hand still.

"Leaving," Rory announced, heading to the closest section to her where she'd taken a book from.

Tristan kept up with her. When he saw that she was putting the book back where she'd originally taken it from, he frowned. "Isn't there some sort of place where you can put your book and they'll put it back for you?" he asked.

Rory nodded.

"Why don't you use it then?"

"I don't see the point of making someone else do something that you're perfectly capable of doing yourself," Rory responded.

"I'm sure that's what you say to your maids back home," Tristan said, guessing that Rory had come from a wealthy family.

"What makes you assume I'm wealthy?" Rory asked. "Is it because I go to an ivy-league school? There are such things as scholarships."

"You went to Chilton as well, if I remember correctly," Tristan said.

"Repeat: there are things such as scholarships."

Tristan thought for a moment. "It's the way you carry yourself. You aren't stuck up, but you have this…vibe that…" He trailed off, not finding the words to express what he was trying to say.

"Really? I have a vibe?" Rory asked. "Can you read the vibe I'm sending to you right now?"

Tristan was silent.

"Wow, you actually got that?" Rory started for the door to the library.

Tristan had a delayed reaction and paused for a moment, contemplating what Rory meant by her comment. When it hit him, he quickened his pace to catch up with her. "Rory, wait!"

Rory paused, glancing back at him. She bit her lower lip, as if wondering whether to stay standing their or to quicken her pace towards the car. "I thought we had a vibe connection going on?" She raised an eyebrow, waiting for his response.

At least she was waiting, Tristan thought.

Tristan tried to find words. _Four thousand…four thousand…_ All he had had to do was repeat the number over and over again in his head and it made him determined not to lose. "I can't just leave you alone, although I'm sure that's what you want," Tristan said, "but I think we have another sort of connection too. Want to test it out by going out with me next Friday night?"

A week away, yes, but as far as Tristan was concerned, he still had two weeks left. One date with her and Rory would be a goner. Tristan was pretty sure about it.

Once Rory got past the shock, she started to laugh. She quickly covered her mouth with her hand and tried to muffle it, but it soon become uncontrollable and her shoulders shook. "That's a good one," Rory said. Seeing the scowl on Tristan's face, she tried to stop her laugher, but it was harder than she thought it would be. "Are you…are you…are you actually serious?"

Tristan's scowl grew. "What's so funny about me asking you out?"

"I thought you were joking!" Rory exclaimed. "Like this was just some kind of bet you made with one of your pals. 'Get the studious girl to say yes.'"

Tristan's eyes grew, scowl gone, and he tried to disguise the shock, but it went away too slowly.

"What? This is some sort of bet? _With who_?"

"No, it's not a bet at all. I'm just…surprised that you would even think that. Do you know how gorgeous you are?"

Rory eyed him, as if trying to tell whether or not he was lying. She just shrugged and said, "Don't take it too personally when I decline the invitation. I'd be lying if I were to say that it wasn't you…"

Rory then turned and walked out towards her car, not looking back at Tristan.

Tristan numbly walked back to where Michael was sitting. "I think…I got my first rejection," he said, in shock.

Michael started to grin, but upon seeing the look on Tristan's face, he held it back. "It's harder than you thought it would be, huh?"

Tristan didn't feel like lying so he just put his head down on the table and pretended like he didn't hear Michael's comment.

---

Once in the car, Rory grabbed her cell phone and dialed Mallory's phone number. Mallory answered on about the fifth ring, just as Rory was about to give up.

"Sorry…" Mallory said, letting a little giggle slip out. "I was a bit… 'busy', if you know what I mean." She let out another giggle.

"Oh god! Not needed information! Why are you even answering the phone then?"

"Hmm, Erik's not that good," Mallory said with a laugh.

"HEY!" Rory hear Erik's voice protest in the background.

"Sorry, I'll let you…get back to what you were doing," Rory apologized.

"No, that's fine; what's up?"

"It's real quick," Rory reassured her. "There wouldn't happen to be any bet out about me that you'd know about?"

Mallory was silent for a moment. "No, nothing I know about. What's up, sweetie? Why would you think that?"

"Tristan Dugrey asked me out," Rory spit out bitterly. "I asked if it was a bet and I wouldn't be surprised by his action. And frankly, I was hoping it was a bet."

Mallory let out a nervous laugh. "Nope, no bet I know about. I should get back to Erik though, but I'll come in and see you when I get back tonight."

"Okay, sorry for interrupting," Rory apologized again.

"Oh, don't worry about it. You can call anytime," Mallory reassured her.

"Just next time the phone will be turned off," Rory heard Erik mumble.

Rory laughed. "See you later."

Mallory returned the sentiments before closing her cell phone. Erik rolled back on top of her and began to kiss her neck, one hand sneaking his way under her shirt and the other onto her thighs.

"Hey, stop that," Mallory protested. "Rory just asked me if there was some sort of bet on her."

Erik stiffened for a moment, but just grinned. "If she's suspicious then all the better, it just makes it harder for T."

Mallory frowned. "I don't know if I like this side of you. Why can't you just do the right thing and call it off? Rory is _my_ friend and I don't want her to be the target of any bet, _especially_ your bet."

"You don't understand, Mal," Erik said. "But let's not talk about it tonight."

Mallory shook her head as he bent back down to kiss her. "I think I'll just take off now," she said. "I really don't feel like doing anything with you if you won't even talk."

"Mal, don't act like this."

Mallory bent over and kiss his cheek as she slipped into her sandals that were lying on the floor beside the bed. "Just for the record, I'm not mad at you; I'm disappointed. But if this bet continues and Rory gets hurt in any way, shape, or form, I will be beyond pissed."

"Duly noted," Erik said dryly. He got up and headed towards the bathroom.

"Where are you going?" Mallory asked.

"Cold shower," was all Erik said before disappearing into the room.

When Mallory got back to the doors, she found Rory in the common room, flipping through channels. She set her keys on the table beside the drawer and walked over towards Rory, settling down on the couch beside her.

"Anything good on?" she asked.

Rory shook her head and then asked, "Back so soon?"

"The mood was sort of ruined," Mallory explained. When she felt Rory begin to apologize again, she held up her hand. "Not your fault, just other stuff. But what do you say you pick out a movie and I'll go make us some popcorn?"

Rory raised an eyebrow. "We're going to need more than popcorn."

So a movie was picked, popcorn was made, a pizza was ordered, and a variety of junk food was spread across the table but while the movie was playing during their "girl bonding time" Rory began to think about Tristan and his odd proposal.

_We had a connection? Yeah_ Right.

* * *

**Author's note:**

I am _so_ sorry about the long time it took to update. It didn't even feel like it was that long so I apologize profusely. This chapter was hard to write because really, I have no clue where I want this story to go. Sure, ultimately, I know, but the little steps are a bit hazy for me. I don't quite want Rory to say yes to Tristan yet, but its hard coming up with little chance encounters (or not so chanced, like the Erik informing Tristan on the library) and still keeping you guys satisfied with all the other characters that make up the story. Ideas, suggests, etc. are welcome so if you have any, please share. :)

**Thanks for reviewing: **

**emmy** (Thanks for saying I'm a great writer! And for noticing the stars…you were one of two.), **Danger1Zone1988** (No, Dean is not quite gone yet. And patience, this is only the seventh chapter. It'll happen soon enough),** LoVe23**,** riotgirllina, princetongirl**,** karahbella**,** i die without you**,** Lalalaaaa**,** jalna**,** eternalgorithm** (Thanks for replying—just let me know if you think my story is progressing too slowly, though!), and** TristenLover** (thanks for reading the note!).


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